


First

by Hoodoo



Category: School of Rock (2003), School of Rock - Lloyd Webber/Slater/Fellowes
Genre: Explicit Sexual Content, F/M, Fingerfucking, First Time, Loss of Virginity, Penis In Vagina Sex, Sexual Inexperience, Sweet/Hot, Vaginal Fingering, Vaginal Sex, Virginity, soft and slow, too quick
Language: English
Status: Completed
Published: 2020-10-22
Updated: 2020-10-22
Packaged: 2021-03-09 03:42:02
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,050
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/27147517
Author URL: https://archiveofourown.org/users/Hoodoo/pseuds/Hoodoo
Summary: Dewey is your first.
Relationships: Dewey Finn & Reader, Dewey Finn/Original Female Character, Dewey Finn/Reader
Comments: 4
Kudos: 29





	First

“What about tonight?”

Dewey pulled away from your mouth, an action made more difficult because he was pinned to your couch while you sat atop him so there wasn’t much room to move his head. He looked up at you with dark eyes.

“What about tonight?” he repeated back at you, as if for clarification.

“What if … what if …” You had unnatural pauses in your breath; you were aroused and when did it get to be so hot in here? “What if tonight’s the night? And we … you know. You and me …?”

You didn’t finish the sentence. You didn’t need to. 

“What? Are you sure?” Dewey asked before checking his obvious excitement, knowing how concerned you’d been with the whole idea of actually ‘going all the way’, as if using teenager’s euphemisms made it more palatable. Still, his hands tightened under your thighs. “I mean, it’s up to you, baby.”

It’d been a good evening together. A nice meal, a pleasant walk home, a forgettable movie on the TV that you didn’t need to pay attention to–-which was important, because somewhere between Dewey laying his head in your lap and you running your fingers through his hair, he’d planted a kiss on your wrist that lead to you contorting enough to kiss him his face and then somehow positions had been switched and you were now straddling his legs and still running your fingers through his hair but face to face with him and your tongue was in his mouth. 

This was something that had weighed on your mind. You’d never been cagy about telling your boyfriend–-even just that word left a tingle in your stomach!-–that your experience in physical intimacy was limited compared to what you imagined other people your age had. Dewey had nodded as you told him, but didn’t judge. 

The times the two of you had edged closer to that territory-–he’d cupped his hand over your pussy and you’d given him a very amateurish handjob, once–-you’d halted it. To his credit Dewey never pushed you and respected your boundaries, even when it got hot and heavy and he definitely had an erection and most likely took a cold shower when he got home.

So the odd combination of excitement but reservation was to be expected. 

“I’m sure,” you told him, with a dry throat. You didn’t add that your body was sure, it was just your mind that seemed to want to hold you back. 

Panting as much as you were, Dewey’s dark eyes searched your face. He didn’t ask for verification again; he simply surged upward to capture your mouth with his. 

You held his jaw to keep him close. His hands squeezed the curve of your ass, his fingers dangerously close to being between your legs from behind. He pulled you to him, leaving no room between your stomach and his, and it was very clear he was hard behind his fly.

“Let’s go to the bed?” he suggested in the lowest voice you’d ever heard from him .

You couldn’t agree fast enough. “Uh-huh-–”

Dewey stood up and grappled you with him, making you shriek in laughter. Begging him to put you down, he didn’t, and as awkward as it was, he carried you all the way to your bedroom, kicking open your door before dropping you like a sack of potatoes to your mattress. 

Still laughing you pulled him down into a playful kiss that took a sharp right turn and became something heady and addictive. Your hands still clutched at his shirt, and in only a few moments you were doing your best to strip him of it, even though you were reluctant to break your mouth away from his. 

He seemed just as eager, his fingers fumbling with the small buttons on the front of your shirt. At least yours could be shoved back over your shoulders versus having to be pulled over your head!

In no time at all, it seemed, the two of you were more naked than not on the mattress. You weren’t sure when your bra came off, and at one point Dewey was hobbled by his jeans that turned inside out as he tried too desperately to kick them off. Once he’d finally shed them properly, you were on your back and he was on his side, hiked up on an elbow. The remaining clothing was underwear; Dewey’s was tented and a wet spot had formed on the cotton in the front. 

He paused to take a breath from the kissing, looking down at you. You watched his eyes travel your body and it was like his gaze was the sun; your skin felt warm all over. With his free hand, he ran just his fingertips over you, from collar bone to navel.

You shivered. 

“We don’t have to go any further,” he said sincerely, and you knew he was assuring you because he’d taken in the sight of your legs still pressed together.

“I know,” you replied, and that was just as truthful. Unlike some of the stories you’d heard from friends about men expecting sex, Dewey had been nothing but patient with you. It did still feel slightly odd that this seemed so deliberate, actually talking about doing it instead of it just happening like it always seemed in the movies. “But … the thing is …”

Dewey raised his eyebrows, waiting for the completion of the sentence. 

“ … the thing is, I _want_ to,” you admitted.

That made him grin, and lean down to kiss you again. 

With his tongue in your mouth as as distraction, he let his hand ease further downward, and his fingertips nudged under the elastic of your underwear. He paused, but besides a light intake of breath you didn’t break the kiss, so his hand continued. Your legs relaxed a little, giving him a bit of space to gently slip his fingers along your pussy.

It felt … interesting to have a different hand there. Dewey’s fingers were lightly calloused but not heavy. He teased you, both by varying the sensations with his mouth and by stroking you lightly. For an inordinate amount of time, it seemed, he didn’t delve deeper until your legs opened a little more.

He gave a smile you felt.

“This’d be easier if your panties were off,” he told you. His voice had dropped register again, and the sheer growl of it made you shiver.

Wordlessly, quickly, before you could think about it too much, you planted your feet, lifted your hips and wiggled out of your panties, flinging them somewhere off the bed.

Dewey’s smile widened as he glanced down at your nudity. You were panting out of a combination of arousal and worry. He saw that, of course, and brought his hand back up a moment to cup one of your tits. Planting a kiss on your chest, he moved his lips to a nipple, capturing it between his lips and flicking it with his tongue. It tightened and the arm under him moved up to grab at his hair as you gasped. 

Again he was achingly slow. It felt good; pleasure radiated out into your chest from the sucking and nipping he graced your nipple with. You were the one to apply pressure by pulling his hair to get him off you for a second. Your nipple was peaked and shiny from spit as he looked up at you.

“Too much?”

You shook your head. “It’s good. I just thought …”

He read your mind. “We’ll get there baby. I know you’re worried, and I wanna make you feel good. But if you insist–”

Dewey winked and made a deliberate show of putting the fingers of his free hand into his mouth, wetting them, before dropping them back down between your legs. The warmth and now the wet made you chuckle, and you thighs moved apart more readily for him.

This time he didn’t merely stroke along your mouth; he allowed his middle finger to slip along your slit, to a more intimate area.

You gasped and jerked, but he didn’t stop. His finger dipped deeper along you, lighting up nerve endings you were familiar with but in a decidedly new way. Although one leg was pressed against the line of his body, the other was free to move so it did, bending at the knee to allow him more access. There was still a part of your mind that would have slowed things down, but your body decided to ignore that and forge its own path, chasing the hint of pleasure. 

With more room and the obvious permission, Dewey drew his fingers along you. You could feel him nudge into a little–not actual penetration, but close–but he also found your clit and just the touch of his fingertip to it made you jump, gasp and moan.

“That’s good,” he cooed.

You managed a smile as a response, that was lost when your jaw when loose when he moved his hand to more completely cover you. That left steady pressure on your clit as his finger finally, carefully, slipped into you. Just a little at first; just enough for you to know it was there. As you tensed, Dewey paused.

“This okay, baby?” he asked.

You lifted your eyes to his to find him waiting for more permission before he did anything else. You licked your lips and nodded, afraid to answer verbally in case you’d lost your voice.

He gave it a few more seconds to give you time to decide no, then gently moved that one finger in deeper. Again the only novel thing was that it was someone else’s hand on you, and one finger wasn’t thick enough to cause any discomfort. Although you had tensed in anticipation, it was easy to let that go. The combined sensations from the easy penetration and the sparks of pleasure at your clit made you moan.

His first movement, a gentle pull and push, made that moan ratchet a bit, but it also elicited a laugh of surprise. You weren’t expecting such light friction to cause such pleasure! Dewey kept the pace of his hand easy, and soon your hips moved along with him, lifting when his hand moved away, pressing down when he was close. Tiny moans filled the air between you, and suddenly it dawned on you that he was moaning too. That made your brow furrow.

“Dewey, I’m not–let me do something to you!” you groaned, because his hand didn’t stop. “What do you want?”

You reached awkwardly across your body to his stomach, lightly scratching it and trying to maneuver your hand to his underwear.

At the touch of your nails dragging down his skin, his eyelids fluttered, but he stopped you before you reached your goal.

“No–wait! Baby, I’m so turned on right now that I won’t last long if you … well, if you do much of anything.”

It gave you a thrill that he was aroused by the simple at of touching you.

“Do you want me to continue?”

You did, but in a heated rush, it wasn’t enough. A primal part of you wanted more, wanted to chase a deeper feeling that somehow you knew was more than a single finger could provide.

“Dewey …”

“Yeah, baby?” he replied, glancing down your body and starting to move his hand again as if it was involuntary.

“Let’s do it.”

His eyes immediately locked on yours again. “Only if you’re sure. Only if you’re ready.”

You nodded a little feverishly. 

Dewey grinned again and dropped his head to kiss you once more. Then he took his hand away–you groaned at the loss–to shuck his briefs. It was a little more coordinated than getting rid of his jeans, but not by much. He flung his underwear off the bed too, like you’d done yours.

Although being trapped behind his briefs had wicked away any precome, a new bead of it formed on the head of his cock, heralding his arousal. Because he’d moved it gave you more room to finally wrap your hand around him. He groaned deeply as you did, the sound vibrating out of his chest.

“D-don’t do much,” he stuttered, even as his breath hitched. “I can’t–-I won’t last long! If you want to go further, please don’t-–”

You interrupted him with a stroke, just to get more familiar with the delicate skin encasing his hardness, but at the cry he made you released him. Looking deeper in color than you remembered from seeing it before, his cock bobbed against his lower belly.

Dewey paused a moment, catching his breath, before opening his eyes again. You kissed him then, so not to surprise him with it, letting your hand roam over him from chest to back to upper thigh to ass, squeezing and lightly scratching along the way. His tongue found yours; that was anchoring. Something familiar. You’d enjoyed when he touched you between the legs, and a deeper heat was building.

When the kiss broke you smiled at him, and with a grip on his hip, you pulled him a little, to encourage him up. As he complied, you slipped a leg underneath him so he was between your thighs.

His palms planted on the mattress beside you and holding himself up on his knees, Dewey looked down at you.

“You’re sure?”

His constant checking in and permission-seeking was sweet. Yes, you nodded, then verbalized it to add weight to it.

He took a breath, and nodded too.

“I’ll go slow,” he promised.

With that, he looked down and look himself in hand. The head of it met your pussy, and involuntarily you gulped. Dewey paused again, brought his hand up to his mouth to spit into it, then gave himself a quick stroke to coat his cock with some lubrication. Then he pressed forward again. It didn’t quite seem to connect.

Reaching between the two of you, you took his cock in hand, guiding him to the right spot. He flashed you a grin, then rocked his hips forward.

His finger hadn’t been much, but his cock was s different story. The sensations were amplified: pressure, a slight burn, a friction that you hadn’t expected. You grit your teeth against a cry that wanted out, thinking that if it seemed like you were disliking it, he would stop. It wasn’t the most earth-shattering feeling, like erotica novels proclaimed, but it wasn’t the worst either. Maybe more would be better-–

“More?” Dewey panted.

Oh-–did you say that out loud?! If you had, you couldn’t refute it.

“Yes, yes–please more!” you replied, your words coming between your sharp breaths too.

Dewey complied.

You tried to focus on breathing, on being relaxed. The feeling of someone else inside you, of being so literally naked and open to someone else was heady, and a little unnerving, but before you could spiral down with overthinking it, Dewey stopped. His arms were shaking, and sweat had broken out on his forehead.

He must have thought you wanted him to stop! 

“Dewey, it’s okay, keep going, please--”

He grimaced as if trying to remain calm. “I’m all the way in, baby.”

At his words, you clenched your pussy around him. That didn’t feel bad at all, and he groaned.

“Jesus!” he croaked, then, “You okay? This okay?”

“Y-yes–”

“Oh god, baby, this feels so good. I’m gonna move, okay?”

You breathed an affirmative, and wrapped your legs around his waist while your hand went to under his arms to his back. With a shudder, Dewey started.

He wasn’t smooth; his movements seemed shallow and tentative, nothing like the harder thrusts you’d seen in porn. That was okay, however; each pull alit nerve endings and each push opened you back up. The discomfort lessened, and it became so right to have him deep inside you. You weren’t sure how much movement you could do, so stayed relatively still. Dewey panted and moaned and shook; you did too, as pleasure slowly began climbing somewhere behind your navel.

It never had a chance to reach its peak, however. In only a few minutes, Dewey stopped completely, moaning a little with his eyes screwed shut.

“Dewey?” you asked quietly, squeezing your internal muscles around him, because that felt very good. 

“Oh–oh– _I’m going to come-–”_ he gasped, and before you could reply, he jerked away from you, out of you, pushing himself up.

The movement pulled his cock out of your pussy in a harder way than he’d done before, leaving you gasping. Dropping a hand to his cock and groaning, he came. Some of his ejaculate spurted onto your pubic hair, but he was able to catch most of it in his palm. You couldn’t tear your eyes off him, flicking between his throbbing cock and the expression on his face. His brow furrowed and eyes clamped shut, the lingering moan he gave made you groan in the same vicarious pleasure he must have felt when he had been stimulating you.

His tightened expression loosened quickly, and you slipped a hand to the back of his head to pull him down for a kiss. He returned it, but kept his body up and off you as he did.

“Sorry, baby. I didn’t mean for that to be so short,” he murmured. “I didn’t want to come inside you either, I didn’t know how you’d feel about it.”

His consideration while engaged balls’ deep in a pussy made you smile and plant a kiss to the side of his head, above his ear.

“That’s okay,” you assured him.

Carefully, he sat back and moved from between your legs, stretching to grab a tissue from the box on the table beside the bed.

“I’m sorry it was so short,” he apologized again. “You didn’t get a chance to come …”

“It’s okay.” Truthfully, from what you’d heard, you expected the whole thing to be more painful than not, so the fact that it was only mildly uncomfortable and you did feel some pleasure was a win in your mind. “We’ll have lots of time to figure it out, right?”

“Right!” he agreed enthusiastically, and flopped down beside you again, kissing you through your laughter. 

_fin!_


End file.
